Allyl Alcohol → HCID 18365121, compound

HRID 380449Notes

Reaction equation

HRID 380449 reaction equation
[Na].[CH2:2]([OH:5])[CH:3]=[CH2:4].[Cl:6][C:7]1[N:15]=[C:14]2[C:10]([NH:11][CH:12]=[N:13]2)=[C:9](Cl)[N:8]=1>C(O)(=O)C>[CH2:2]([O:5][C:9]1[N:8]=[C:7]([Cl:6])[N:15]=[C:14]2[C:10]=1[NH:11][CH:12]=[N:13]2)[CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 53244122,6-DichloropurineHCID 5360545Sodium

Product 1

HCID 18365121HCID 18365121, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium (0.37 g, 15.9 mmol) was reacted with allyl alcohol (20 ml) under nitrogen with cooling in an ice bath. 2,6-Dichloropurine (1.00 g, 5.29 mmol) was added and the reaction was refluxed for 2 h, after which time the reaction mixture was allowed to cool. The mixture was neutralised with glacial acetic acid and the solvent was removed. The residue was triturated with cold water to yield the title compound as a white solid (1.05 g, 94%), m.p. 208-209° C.; νmax (cm−1) 3422,3017, 2782, 2685, 2595 (NH, C—H); δH (200 MHz, d6-DMSO) 8.454 (1H, s, C(8)H), 6.230-6.036 (1H, m, CH2CH═CH2), 5.478 (1H, dd, J=1.6 Hz, J=17.2 Hz, CH2CH═CH2), 5.327 (1H, dd, J=1.6 Hz, J=10.4 Hz, CN2CH═CH2), 5.054 (2H, d, J=5.5 Hz, CH2CH═CH2); m/z 210 (M+, 68%), 195 (64), 183 (12), 175 ([M—Cl]+, 98%), 154 ([MH—OCH2CH═CH2]+, 21%), 135 ([MH—Cl—CH2CH═CH2]+, 50%), 119 ([MH—Cl—OCH2CH═CH2]+, 33%), 92 (12), 53 (18), 41 ([CH2CH═CH2]+, 100%), 32 (53).

Workup

  1. temperaturewith cooling in an ice bath
  2. temperaturethe reaction was refluxed for 2 h
  3. temperatureto cool
  4. customthe solvent was removed
  5. customThe residue was triturated with cold water

Sources & evidence

ORD record
ord-b7440358ca2241e2a984898126cf250d
Source dataset
uspto-grants-2001_10
Patent number
US06303618B1

Reaction notes

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